Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:37 UTC |
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Update date | 2019-11-26 02:55:00 UTC |
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Primary ID | FDB000565 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | alpha-Tocopherol |
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Description | Constituent of many vegetable oils such as soya and sunflower oils. Dietary supplement and nutrient. Nutriceutical with anticancer and antioxidant props. Added to fats and oils to prevent rancidity. The naturally-occurring tocopherol is a single stereoisomer; synthetic forms are a mixture of all eight possible isomers
Alpha-tocopherol is traditionally recognized as the most active form of vitamin E in humans, and is a powerful biological antioxidant. alpha-Tocopherol is found in many foods, some of which are custard apple, nopal, bitter gourd, and kumquat. |
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CAS Number | 59-02-9 |
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Structure | |
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Synonyms | Synonym | Source |
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(+)-alpha-Tocopherol | ChEBI | (2R)-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol | ChEBI | (2R,4'r,8'r)-alpha-Tocopherol | ChEBI | (all-R)-alpha-Tocopherol | ChEBI | 5,7,8-Trimethyltocol | ChEBI | D-alpha-Tocopherol | ChEBI | RRR-alpha-Tocopherol | ChEBI | Vitamin e | ChEBI | (+)-a-Tocopherol | Generator | (+)-Α-tocopherol | Generator | (2R,4'r,8'r)-a-Tocopherol | Generator | (2R,4'r,8'r)-Α-tocopherol | Generator | (all-R)-a-Tocopherol | Generator | (all-R)-Α-tocopherol | Generator | D-a-Tocopherol | Generator | D-Α-tocopherol | Generator | RRR-a-Tocopherol | Generator | RRR-Α-tocopherol | Generator | a-Tocopherol | Generator | Α-tocopherol | Generator | (R,R,R)-alpha-Tocopherol | ChEBI | (R,R,R)-a-Tocopherol | Generator | (R,R,R)-α-Tocopherol | Generator | (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol | HMDB | a-D-Tocopherol | HMDB | alpha-delta-Tocopherol | HMDB | delta-alpha-Tocopherol | HMDB | Denamone | HMDB | Eprolin | HMDB | Phytogermin | HMDB | Phytogermine | HMDB | RRR-alpha-Tocopheryl | HMDB | Vitamin ea | HMDB | alpha-Tocopherol | ChEBI | (+)-2R,4'R,8'R-alpha-Tocopherol | HMDB | (+)-2R,4'R,8'R-α-Tocopherol | HMDB | (+)-2R,4’R,8’R-α-Tocopherol | HMDB | (2R,4’R,8’R)-α-Tocopherol | HMDB | 3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-(2R)-2H-1-benzopyran-6-ol | HMDB | alpha-D-Tocopherol | HMDB | alpha-Vitamin E | HMDB | α-D-Tocopherol | HMDB | α-Vitamin E | HMDB | Almefrol | PhytoBank | Emipherol | PhytoBank | Etamican | PhytoBank | Evitaminum | PhytoBank | Profecundin | PhytoBank | Vitamin Ealpha | PhytoBank | Vitamin Eα | PhytoBank | (+)-a-tocopherol | biospider | (+)-alpha-tocopherol | biospider | (+)-α-tocopherol | Generator | (2R,4'R,8'R)-a-Tocopherol | biospider | (2R,4'R,8'R)-alpha-Tocopherol | biospider | (2R,4'R,8'r)-α-tocopherol | Generator | (2R)-3,4-dihydro-2,5,7,8-Tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol | HMDB | (all-r)-a-tocopherol | biospider | (r,r,r)-a-tocopherol | biospider | (r,r,r)-alpha-tocopherol | biospider | (R,R,R)-α-tocopherol | Generator | 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol, 9CI | db_source | a-tocopherol | biospider | Alpha-delta-tocopherol | biospider | Alpha-tocopherol | biospider | Antisterility vitamin | db_source | Covitol | biospider | D-alpha-tocopherol | biospider | D-α-tocopherol | Generator | Delta-alpha-tocopherol | biospider | E307 | db_source | Ephanyl | biospider | Ephynal | db_source | Natopherol | biospider | RRR-alpha-tocopherol | biospider | RRR-alpha-tocopheryl | HMDB | Syntopherol | db_source | Tocopherol | biospider | Vitamin E? | db_source | α-tocopherol | Generator |
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Predicted Properties | |
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Chemical Formula | C29H50O2 |
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IUPAC name | (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol |
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InChI Identifier | InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1 |
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InChI Key | GVJHHUAWPYXKBD-IEOSBIPESA-N |
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Isomeric SMILES | CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C |
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Average Molecular Weight | 430.7061 |
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Monoisotopic Molecular Weight | 430.381080844 |
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Classification |
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Description | Belongs to the class of organic compounds known as tocopherols. These are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Quinone and hydroquinone lipids |
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Direct Parent | Tocopherols |
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Alternative Parents | |
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Substituents | - Tocopherol
- Diterpenoid
- 1-benzopyran
- Benzopyran
- Chromane
- Alkyl aryl ether
- Benzenoid
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 80.87%; H 11.70%; O 7.43% | DFC |
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Melting Point | Mp 2.5-3.5° | DFC |
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Boiling Point | Bp0.03 140° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]25D +0.65 (EtOH) | DFC |
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Spectroscopic UV Data | [neutral] lmax 292 () (EtOH) (Berdy) | DFC |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-0159-2900500000-03e8a824731610752eb3 | 2014-09-20 | View Spectrum | GC-MS | alpha-Tocopherol, 1 TMS, GC-MS Spectrum | splash10-000i-1390000000-fc8c4f9b9405598ede7f | Spectrum | GC-MS | alpha-Tocopherol, 1 TMS, GC-MS Spectrum | splash10-00dr-9150010000-c4abc0e689e9b2476b9d | Spectrum | GC-MS | alpha-Tocopherol, 1 TMS, GC-MS Spectrum | splash10-0f79-1190040000-663296a69129a59be1a6 | Spectrum | GC-MS | alpha-Tocopherol, non-derivatized, GC-MS Spectrum | splash10-000i-1390000000-fc8c4f9b9405598ede7f | Spectrum | GC-MS | alpha-Tocopherol, non-derivatized, GC-MS Spectrum | splash10-00dr-9150010000-c4abc0e689e9b2476b9d | Spectrum | GC-MS | alpha-Tocopherol, non-derivatized, GC-MS Spectrum | splash10-0f79-1190040000-663296a69129a59be1a6 | Spectrum | Predicted GC-MS | alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0aor-9886300000-b3225facac6ebdd8ddbd | Spectrum | Predicted GC-MS | alpha-Tocopherol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000l-7735900000-1585eb83c1211ebe95f2 | Spectrum | Predicted GC-MS | alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | alpha-Tocopherol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-9600100000-aaf885290800a10d3fb2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-01wr-9300000000-f0c814976a58a9d837ca | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0f79-1494700000-6b5f8f817c5a5429ed70 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-EBEB (JMS-HX/HX 110A, JEOL) , Positive | splash10-00lr-4910600000-1eda05dacf9642d7cea0 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-014i-0900000000-a5860634bfd1ceb6833f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0159-0900500000-5a3bc17152cb61859b2c | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0842900000-f51286676592fd184193 | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-1920000000-1994f86bec2bb4a77b9c | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-066r-3930000000-02190bf16d5d85d44bce | 2017-07-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0110900000-c3541294fc60a7a8cc7e | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01t9-0730900000-553c4898757f6876036c | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03e9-0920200000-276273a531fed5b3a2b0 | 2017-07-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-3013900000-4985082235edff7c4b8c | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05r1-9313200000-cbc230d5dd20c629ffab | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9320000000-5958d2e1d5b687b012c1 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000900000-d3ddef81c134412455e1 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0310900000-30597e14cf876e4e4764 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-08g0-2982400000-371737325df4dbb523b2 | 2021-09-22 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 14265 |
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ChEMBL ID | CHEMBL47 |
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KEGG Compound ID | C02477 |
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Pubchem Compound ID | 14985 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00163 |
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HMDB ID | HMDB01893 |
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CRC / DFC (Dictionary of Food Compounds) ID | BDR14-R:BDR14-R |
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EAFUS ID | Not Available |
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Dr. Duke ID | ALPHA-TOCOPHEROL |
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BIGG ID | 2296507 |
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KNApSAcK ID | C00007366 |
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HET ID | VIV |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Alpha-Tocopherol |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti-Alzheimeran | 52217 | An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders. | DUKE | Anti anginal | 52217 | An agent that reduces angina symptoms by improving blood flow to the heart, commonly used in managing angina pectoris, coronary artery disease, and other cardiovascular conditions, to alleviate chest pain and prevent cardiac complications. | DUKE | Anti-arthritic | 52217 | An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life. | DUKE | Anti-asthmatic | 49167 | An agent that relieves bronchospasm and inflammation, commonly used to manage asthma symptoms, chronic obstructive pulmonary disease (COPD), and other respiratory disorders, improving lung function and overall respiratory health. | DUKE | Anti-atherosclerotic | 38070 | An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes. | DUKE | Anti-cancer | 35610 | An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival. | DUKE | Anti-cataract | 52217 | An agent that prevents or slows the formation of cataracts, reducing oxidative stress and inflammation in the lens of the eye, commonly used to manage age-related cataracts and other ocular disorders. | DUKE | Anti convulsant | 52217 | An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain. | DUKE | Anti-dementia | 52217 | An agent that slows or prevents cognitive decline, reducing symptoms of dementia. It plays a biological role in neuroprotection, enhancing neuronal function and survival. Therapeutically, it is used to manage Alzheimer's disease, vascular dementia, and other neurodegenerative disorders, improving memory, cognition, and daily functioning. | DUKE | Anti-diabetic | 52217 | An agent that regulates blood sugar levels, enhancing insulin sensitivity or secretion. Therapeutically, it's used to manage diabetes, reducing symptoms and complications, and commonly prescribed to treat type 1 and 2 diabetes, as well as gestational diabetes. | DUKE | Anti-infarctal | 52217 | An agent that reduces myocardial infarct size, protecting against cardiac damage. It plays a biological role in inhibiting apoptosis and inflammation, promoting therapeutic applications in cardiovascular disease management, and is used to treat conditions such as myocardial infarction, heart failure, and cardiac arrhythmias. | DUKE | Anti-infertility | 52217 | An agent that enhances reproductive health, promoting fertility and conception. Its biological role involves regulating hormonal balance and improving reproductive function. Therapeutically, it is used to treat infertility disorders, with key medical applications in assisted reproduction, polycystic ovary syndrome (PCOS), and unexplained infertility. | DUKE | Anti-ischemic | 52217 | An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload. | DUKE | Anti-maculitic | | An agent that reduces macular inflammation, commonly used in managing age-related macular degeneration and diabetic macular edema, promoting vision preservation and reducing disease progression. | DUKE | Anti-mutagenic | | An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects. | DUKE | Anti neuropathic | | An agent that relieves symptoms such as pain, numbness, and tingling caused by damage or disease affecting the somatosensory nervous system, commonly used in managing conditions like diabetes, shingles, and nerve injuries. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Anti-Parkinsonian | 48407 | An agent that alleviates symptoms of Parkinson's disease, enhancing dopamine levels and improving motor function, commonly used to manage tremors, rigidity, and bradykinesia in neurodegenerative disorders. | DUKE | Anti radicular | | An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management. | DUKE | Anti-retinotic | | An agent that inhibits retinoic acid activity, acting as a receptor antagonist. It plays a biological role in regulating cell growth and differentiation. Therapeutically, it has applications in managing retinoic acid-related disorders, with key medical uses including treatment of retinoic acid toxicity and certain types of cancer. | DUKE | Anti-rheumatic | 52217 | An agent that reduces inflammation and alleviates symptoms of rheumatic diseases, such as arthritis. It plays a biological role in modulating the immune system and inhibiting pro-inflammatory pathways. Therapeutically, anti-rheumatics are used to manage conditions like rheumatoid arthritis, lupus, and osteoarthritis, reducing pain, swelling, and joint damage. Key medical uses include slowing disease progression and improving quality of life for patients with chronic rheumatic conditions. | DUKE | Anti-stroke | 52217 | An agent that prevents or reduces the severity of stroke, typically by inhibiting blood clot formation or improving cerebral blood flow, commonly used in managing cardiovascular diseases, preventing stroke recurrence, and reducing stroke-related brain damage. | DUKE | Antitumor | 35610 | An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes. | DUKE | Antitumor promoter | 35610 | An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis. | DUKE | Cancer preventive | 35610 | An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence. | DUKE | Cardioprotective | 38070 | An agent that protects the heart from damage, reducing the risk of cardiovascular disease. It plays a biological role in mitigating cardiac stress and injury, with therapeutic applications in preventing heart attacks, strokes, and arrhythmias, and key medical uses in treating hypertension, heart failure, and coronary artery disease. | DUKE | Circulotonic | | A cardiac stimulant that enhances cardiovascular function, increasing cardiac output and blood pressure. Therapeutically, it's used to treat hypotension, shock, and heart failure, improving circulation and overall cardiovascular health. Key medical uses include managing cardiogenic shock, post-operative hypotension, and severe dehydration. | DUKE | Immunomodulator | 50846 | An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Nuclear receptor subfamily 1 group I member 2 | NR1I2 | O75469 | Glutamate--cysteine ligase catalytic subunit | GCLC | P48506 | Glutathione S-transferase Mu 3 | GSTM3 | P21266 | Glutathione S-transferase omega-1 | GSTO1 | P78417 | Glutathione S-transferase A2 | GSTA2 | P09210 | Glutathione S-transferase P | GSTP1 | P09211 | Serine palmitoyltransferase 1 | SPTLC1 | O15269 | Alpha-tocopherol transfer protein | TTPA | P49638 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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